(2R,3R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl hydroxycarbamate | 1316852-30-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R,3R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl hydroxycarbamate
• 英文别名: [(2R,3R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,6-dihydro-2H-pyran-3-yl] N-hydroxycarbamate
• CAS: 1316852-30-8
• 化学式: C₁₃H₂₅NO₅Si
• 分子量: 303.431
• InChiKey: CGXIWBFUVRTWNN-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl hydroxycarbamate 在 咪唑 、 potassium osmate(VI) dihydrate 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 17.0h， 生成 (3aR,4R,7S,7aS)-7-((tert-butyldimethylsilyl)oxy)-4-(hydroxymethyl)-1-methyltetrahydro-1H-pyrano[4,3-d]oxazol-2(6H)-one
  参考文献：
  名称：

  Synthesis of the dysiherbaine tetrahydropyran core utilizing improved tethered aminohydroxylation conditions

  摘要：

  A concise stereoselective route to the dysiherbaine tetrahydropyran core was achieved in nine steps and 39% overall yield. Donohoe's improved tethered aminohydroxylation conditions were employed to concurrently install the amino and alcohol groups and construct the tetrahydropyran ring, which features four contiguous cis-stereocenters. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.106
• 作为产物：
  描述：

  N,N'-羰基二咪唑 、 (2R,3R)-2-[(tert-butyldimethylsilanyloxy)methyl]-3-hydroxy-3,6-dihydro-2H-pyran 在 吡啶 、 盐酸羟胺 作用下， 反应 26.0h， 以60%的产率得到(2R,3R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,6-dihydro-2H-pyran-3-yl hydroxycarbamate
  参考文献：
  名称：

  Synthesis of the dysiherbaine tetrahydropyran core utilizing improved tethered aminohydroxylation conditions

  摘要：

  A concise stereoselective route to the dysiherbaine tetrahydropyran core was achieved in nine steps and 39% overall yield. Donohoe's improved tethered aminohydroxylation conditions were employed to concurrently install the amino and alcohol groups and construct the tetrahydropyran ring, which features four contiguous cis-stereocenters. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.106

文献信息

• Synthesis of the dysiherbaine tetrahydropyran core utilizing improved tethered aminohydroxylation conditions
  作者：Christopher L. Carroll、A. Richard Chamberlin

  DOI：10.1016/j.tetlet.2011.05.106

  日期：2011.8

  A concise stereoselective route to the dysiherbaine tetrahydropyran core was achieved in nine steps and 39% overall yield. Donohoe's improved tethered aminohydroxylation conditions were employed to concurrently install the amino and alcohol groups and construct the tetrahydropyran ring, which features four contiguous cis-stereocenters. (C) 2011 Elsevier Ltd. All rights reserved.